Stephen Warley runs a community and weekly podcast called Life Skills That Matter. He believes work as we know it is changing. Stephen is on a mission to spread that message and help people prepare for it.

Important Highlights and Takeaways

Self-employment is a more natural way of being human and being 100% yourself

Trying self-employment for a year will teach you more than you ever imagined

Working for yourself makes you more attractive to future employers should you decide that self-employment is not for you

Working for yourself is a shift in self-identity

The hardest question you’ll ever answer for yourself is “What do I want?”

The industrial revolution let us put off thinking about and getting clear about what we really want

Technology we have created is now forcing us to answer it

What we really want will translate into the work we do

If you are feeling overwhelmed by a big project or a dream you have, write out a recipe for you what you think is involved:

What are all the ingredients you think you need?

What do do you think the steps are?

Who can you ask for help?

What’s the smallest next step you can take (even if it feels too small)?

You are self-employed the minute you decide to work on your own terms

Make calendar appointments with yourself–YOU are your most important customer

Be aware of past failings or disappointments you may be interpreting the future with

Looking at John’s next step as an “experiment” opened up so many new possibilities because there could be no “failure”

This is the future of work

Increasing uncertainty will require continuous iteration

Self-reflection becomes an important part of this process as well

Each week Stephen checks in with himself (self-reflection) to evaluate what is working and what is not working

If experiencing a series of negative thoughts, write them all out and get clear on what’s going on

1 Comment

I guess the only thing I might add to this is that self employment never promises one to make a lot of money. Very few of us do. The success stories are rare and just because your friend Joe Schmuck made it big doing what you do, doesn’t mean you will. Most of us struggle month to month to pay our bills. So there is a tradeoff between loving what you do and actually being able to live on it. This especially comes true with the health care bills. My health insurance has always been the most expensive part of the budget and that doesn’t include paying for $5000 deductable before insurance kicks in. T he premiums were up to $800 a month…So if one is willing to live a frugal life, at least for awhile, then by all means go for it. But if one has $2500 house payments and enjoys $10 health insurance co-pays, and 3 week paid vacations, then there is an abrupt awaking ahead.

I love what I do, I love the flexible schedule (working Saturdays and holidays for no extra pay) and all the company perks (being sick with no sick pay, no Christmas bonus, no paid holidays nor vacation, no overtime, no company healthcare plan, no IRA matching contributions, pay all SS percentage). But I do sleep in my own bed every night which I didn’t do with the shop I worked for. I was able to watch my kids grow up instead of being a weekend dad.

So I think the resources you mention about money are super important to the formula of whether to quit and work for yourself. Because if, after a year, and it doesn’t work out, you may be broke and can’t find a job right away. So having a LOT of money in the bank will be a first consideration. It took me 6 months to break even and I burned through about $12,000 ($1980s dollars) of my money trying to start the business. I have heard that it can take 12 to 24 months to become profitable.

Also, there is the time issue. Starting a business is all absorbing. It takes all waking hours. You think about it all the time. It’s like another marriage and trying to keep up 2 of those happy, when doing one right is hard enough. State and Fed. quarterly estimated taxes need to be paid, and that money needs to be saved in order to pay it, a mistake I made the first few quarters. This needs to be done correctly or penalties will be accessed. If one sells a product, then sales tax needs to be calculated, kept and sent in quarterly. Hire someone and then there are all the forms and taxes that need to be sent in quarterly. There may be professional fees due and ongoing classes that need to be paid for and forms to fill out and sent in yearly. It all takes time, time, time. If you think that once you are out from under thumb of the boss, that your time will be your own, it’s not true. I found that every client was a boss and there were times I had 10 bosses instead of one. And all 10 expected me to produce. So working for yourself is actually an oxymoron, because you now work for the customer and he is the boss. Don’t please them and you get fired, just like any other place of employment.

In my trade (and I think this applies to any skill set), there were a LOT of people who could do the work but a lot less knew about the business side of things and got into trouble with taxes and filing govt. reports and not saving for down times. And I sense this is universal problem, not just in the building trades. They went broke, not because they didn’t know their trade well, but because they were ignorant as to what was required once they got paid. All that money is not yours to keep and spend on food and housing and that’s where I got into trouble. After all that, a regular paycheck seems pretty nice, regardless of what problems are at work. No amount of loving what you do will pay the bills. If you are going solo just because you don’t like your boss, you need to reassess your motives. Because you might hate working for yourself. There is a difference between leaving and going. “Leaving” a job doesn’t solve problems, because the problem may be you. “Going” to self employment may energize you, but has its own set of problems, all of which land on your shoulders.

So I add this to what John has said above. Read a lot, educate yourself, do lots of research, talk to self employed people to see what this venture is all about. I’m not advocating not to take the plunge, just do it in an intelligent manner.

So jump in, the water’s fine, it’s just there is this huge drain at the bottom that creates this horrible sucking sound and if you aren’t fully aware and trained in all the facets of swimming, you won’t stay above water very long.